Startup to Last

By Rick Lindquist and Tyler King

What's Startup to Last about?

Two founders talk about how to build software businesses that are meant to last. Each episode includes a deep dive into a different topic related to starting, growing, and sustaining a healthy business.

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Startup to Last episodes:

06.25.2024
Pick one thing and max it out
In this episode, we talk about how the job of an entrepreneur isn’t to decide which ideas are good and which are bad. It’s to pick the single best idea out of a sea of good ideas.
06.06.2024
Step on the gas, or pull back?
In this episode, we talk about a decision Rick needs to make with LegUp Health. Should he treat it like a high-growth startup, or a lifestyle business?
05.16.2024
We ain't talking about zero to one
In this episode, we talk about how a lot of startup advice is focused on businesses going from zero to one, and how we have to be careful not to assume that all applies to us.
05.09.2024
Forms forms forms
In this episode, we talk about Less Annoying CRM’s new form builder, and what it means for the business
04.25.2024
Leveling up the team
In this episode, we discuss using consultants to level up your team.
04.11.2024
The first step of a flywheel
In this episode, Rick explains how he’s getting more hands on with marketing.
03.28.2024
Sometimes you need to touch the hot stove
In this episode, we discuss how some lessons can't be taught, they have to be learned through experience. What does that mean for mentoring less experienced employees?
02.29.2024
When to outsource
In this episode, we talk about when it makes sense to outsource work to contractors and agencies, vs when it makes sense to do something in-house.
02.15.2024
Talk to sales
In this episode, we talk about Less Annoying CRM’s latest sales experiment.
02.01.2024
Learnings from a few days of snowboarding
In this episode, we talk about takeaways from big snow tiny conf, and more.
01.18.2024
Profit first
In this episode, we discuss how Rick is using the “profit first” mindset to manage company finances.
12.29.2023
Looking back at 2023 and forward to 2024
This is our yearly recap episode! Personal updates from 2023TylerGoals from last year
12.15.2023
DEI isn't dead
In this episode, we talk about Rick's open enrollment experience, and what LACRM is doing related to DEI (diversity, equity, and inclusion)
12.01.2023
Growth is hard
In this episode, Rick tries to explain to me that there are people who know how to grow businesses, and I stubbornly insist otherwise.
11.09.2023
Inflection point
In this episode, we discuss what feels like an inflection point in Rick's business. Full topic list:LegUp Health has a new website.Rick thinks he's feeling an inflection point.We daydream about the future of LegUp Health a bit.Things are calm at...
10.27.2023
Reducing Friction
This week, we discuss how LegUp Health reduced a major point of friction when selling to employers. Here's the full topic list:Rick is finally in his new house, and a major stress has been removed.Rick gives updates on LegUp Health,...
10.13.2023
Build it and they will come
In this episode, we discuss whether or not building features customers ask for is a valid path toward growth. Here are all the topics:LACRM has started migrating to Paddle.LegUp Benefits has its first official customer!We discuss how LACRM's free trial...
09.28.2023
The pricing change I didn’t want to make
This week, we talk about a pricing change we recently announced at Less Annoying CRM. We dive into the history behind the decision, how it was communicated, what it means for the finances of the business, and more.
08.31.2023
Reorg
In this episode, we discuss a hodgepodge of things including a company reorg, growth tactics, and more. Here are all the topics:Rick updates us on LegUp Health's progress. He talks about working on the sales pitch, building momentum, staying focused,...
08.15.2023
Execution eats strategy for breakfast
In this episode, we talk about how both of us are refocusing on execution. Here's the full topic list:Tyler is trying to focus everyone at LACRM on the top priorities including:Having the devOps team do a bit more normal software...
07.23.2023
Getting unstuck
In this episode, we talk about Rick’s early signs of success getting out a sales rut, and much more. Full topic list:Rick gives an update on how he and JD are getting out of a sales rut.Rick is busy and...
07.06.2023
You can't optimize nothing
In this episode, we talk about how much optimization should be done before you have demand generation figured out. Here's the full topic list:Rick is back from parental leave, and he has things to say about what it's like to...
06.08.2023
Handling sales tax as a SaaS
In this episode, we talk about what Less Annoying CRM is doing to handle sales tax compliance worldwide. Here are all the topics:Tyler has officially signed the partnership agreement with Rick and LegUp Health!Rick is wrapping up a position/brand/story projectLegUp...
05.26.2023
Recapping the Product Hunt launch
In this episode, we talk about Less Annoying CRM’s producthunt launch, and a lot more. Here's the full topic list:Tyler takes a look back at LACRM's growth history, and explains their new approach to growth.Tyler explains how the recent Product...
04.23.2023
Pivots and renegotiations
In this episode, we discuss some changes to LegUp Health, the end of Tyler's sabbatical, and more. Topics in this episode:Tyler is back from his sabbaticalLACRM is getting ready to launch a major redesignRick gives updates on how the LegUp...
04.03.2023
Yet another podcast about AI
Come on, you know what we're talking about. It's all anyone is talking about. Sorry, we don't make the rules.
03.23.2023
An inside look at building a new product
In this episode, we talk about the very early stages of building LegUp Benefits, and a bunch of other stuff. Topics:Rick has hired a marketing coach for LegUp, and we discuss how to get the team talking to each other...
03.03.2023
How to win against well-funded competitors
In this episode, we talk about how bootstrappers can win against companies that have raised massive amounts of money. Full topic list:We give an update on the compensation negotiations we discussed last episode. We've agreed on terms for Tyler to...
02.17.2023
The one where we negotiate Tyler’s compensation
If you’ve been following along, you know that Tyler is about to temporarily join Rick’s startup to help build their new app. In this episode, we talk about the compensation proposal Rick just came up with. Full topic list:Rick already...
02.03.2023
How we deal with security questionnaires
In this episode, we discuss what we do when a customer has security and compliance questions, plus, a whole lot more. Topics in this episode:Tyler shares his experience at Big Snow Tiny ConfTyler is getting ready for a sabbatical which...
01.20.2023
Something new to announce
Topics this week:Tyler is going to work with Rick to build the new LegUp Benefits SaaS productRick has officially transitioned LegUp to 2023Rick talks about how Airtable Interfaces are usefulRick talks about an annual retreat with JD, and we discuss...
12.31.2022
Looking back at 2022 and forward to 2023
Personal updates from 2022TylerGoals from last year✅ Plan for travel as part of relationship ❌ Build more schedule flexibility Other updatesFigured out personal finance plan with ShellyRickGoals from last year✅ Reprioritize daily personal health habits ❓Spend more quality time with Sable (have a...
12.13.2022
Big bets vs small bets
Topics in this episode: LACRM is having a good DecemberRick is feeling lots of momentumRick gives an update on LegUp Health's growthRick is reading the Warren Buffet bio: The SnowballTyler explains LACRM's new approach to bug triageRick is thinking about how...
12.02.2022
How can founders use the new AI tech?
Topics:Rick gives an update on open enrollmentTyler talks about some upcoming product launches including the new Zapier integrationRick is refining his Adwords approachRick is starting to think about 2023Tyler talks about project managementLACRM had a CRM Coach culture refreshWe talk...
11.11.2022
Professional hater
Topics this week:I mean, Twitter, obviouslyRick gives an update on open enrollment including...Sales so farHis misadventures with Google advertisingWebsite positioning and designTyler gives an update on LACRM's integration projectLACRM just went through a process that happens every six monthsWe talk...
10.27.2022
An opportunity that comes along once per year
Topics from this episode:Rick gives a big update on how LegUp Health is prepping for open enrollmentHis goal is to be long-term patient, but have short-term urgencyHe doesn't have enough traffic for retargetingOutreach will be their main leverThis weekend is...
10.14.2022
What's priority #1?
Topics this week:Tyler is getting ready for Founder SummitRick is learning about digital advertising, and we discuss whether tracking people on the internet is a net good or bad thingTyler gives an update on his NPS sagaTyler talks about a...
09.30.2022
The marketing tech stack
I (Tyler) am traveling and don't have time to write up show notes, so the other topics in this episode are a mystery. Enjoy!
09.16.2022
How much to spend acquiring a customer
Topics this week:Figma got acquired by Adobe AND I DONT WANT TO TALK ABOUT IT I'M NOT CRYING YOU'RE CRYING SHUT UP YOU'RE NOT MY REAL DADRick spent a week in Cancun and soaked up some sweet business wisdomTyler is...
09.02.2022
The great re-org
Topics:LACRM had a great growth month in August, mostly because of expansion revenue.JD, Rick's business partner, is doing a great job.Rick is oscillating between investing in more resources and staying focused.Rick gives an update on his recent local marketing blitz.Tyler...
08.19.2022
Is SaaS getting harder?
Topics this episode:Summer is ending at LACRM and things are going back to normal.Rick attended a company offsite last week, and now he's behind.LegUp Health is planning a local marketing blitz.Tyler gives an update on pay transparency at LACRM.Tyler has...
07.28.2022
Single points of failure
Topics in this episode:LACRM got DDoSed *again*Rick went to some networking eventsTyler is ending his newsletterRick gives a chamber of commerce updateLegUp Health is seeing early success with an incentive offerWe discuss handling an employee who leaves for an extended...
07.14.2022
Should you hire a marketing agency?
Topics in this episode:Less Annoying CRM hit $3.5 million ARR.Rick and LegUp Health have signed up for several in-person networking events as well as a number of chambers of commerce.LACRM had a new CRM Coach start.Tyler reflects on why his...
06.28.2022
Healthy urgency
Topics this week:Tyler thinks he's finally fixed his audio setup.Rick and Tyler are both having good sales months. Rick actually knows why!We discuss what indicators a SaaS company might look at to tell whether a recession is impacting their business.Rick...
06.10.2022
Prioritizing effectiveness over efficiency
Topics from this episode:Rick has learned more about how to be a good business partner.Rick is prioritizing effectiveness over efficiency.Tyler asks about how best to track marketing ROI.Tyler has an idea for a platform play at LACRM.Another company in LegUp...
05.27.2022
Charge Less
Topics from this episode:Rick is working on updating and simplify LegUp Health's messaging.LegUp Health is testing out purchasing leads.Rick talks about the next step of his SEO work.Tyler has been listening to customer interviews and learned some things about pricing...
05.10.2022
Recession?
Topics this weekThe possibility of a recession and how it might impact businesses like ours.LegUp Health just had a competitor acquired.Less Annoying CRM was DDoSed again.Tyler discusses some traction channels he's been considering.Rick asks about virtuous vs. vicious cycles.We discuss...
04.29.2022
How to be a mentor when you aren't knowledgeable about a topic
Topics in this episode:Tyler bought tickets to attend Founder Summit.Tyler is rethinking his investment strategy.A competitor of LegUp Health is going out of business.Tyler is working on renewing LACRM's office lease.LegUp Health is struggling to scale their outreach, so they're...
04.15.2022
Mission, Vision, and Values
Topics this week:A new employee started at LACRMTyler is getting ready for lots of internsRick has been struggling to form healthy habitsRick gives an update on his business partner's work/life balanceTyler finished his cycle of meeting/presentation/1:1s that he does every...
04.01.2022
Tools don't solve problems
Topics this week:Tyler has been extremely busy with meetings, interviews, etc.LACRM hired two new CRM Coaches.Rick took some time off to ski with his family, watched a Duke basketball game, and celebrated his son's 1st birthday.LegUp Health has mixed results...

What's Startup to Last about?

Download our free app to listen on your phone

Startup to Last episodes:

Pick one thing and max it out

Step on the gas, or pull back?

We ain't talking about zero to one

Forms forms forms

Leveling up the team

The first step of a flywheel

Sometimes you need to touch the hot stove

When to outsource

Talk to sales

Learnings from a few days of snowboarding

Profit first

Looking back at 2023 and forward to 2024

DEI isn't dead

Growth is hard

Inflection point

Reducing Friction

Build it and they will come

The pricing change I didn’t want to make

Reorg

Execution eats strategy for breakfast

Getting unstuck

You can't optimize nothing

Handling sales tax as a SaaS

Recapping the Product Hunt launch

Pivots and renegotiations

Yet another podcast about AI

An inside look at building a new product

How to win against well-funded competitors

The one where we negotiate Tyler’s compensation

How we deal with security questionnaires

Something new to announce

Looking back at 2022 and forward to 2023

Big bets vs small bets

How can founders use the new AI tech?

Professional hater

An opportunity that comes along once per year

What's priority #1?

The marketing tech stack

How much to spend acquiring a customer

The great re-org

Is SaaS getting harder?

Single points of failure

Should you hire a marketing agency?

Healthy urgency

Prioritizing effectiveness over efficiency

Charge Less

Recession?

How to be a mentor when you aren't knowledgeable about a topic

Mission, Vision, and Values

Tools don't solve problems

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